My First Experience With Another Guy

by Sean

What’s your gender? Man
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Tutor, tech specialist
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Pansexual
Any other term(s) that describe your sexuality or sexual identity? Fluid and hard to understand really.
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

My First Experience With Another Guy

How long ago did this hookup happen? One year

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He was rather tall, taller than six feet. He had a fair amount of body hair, which I found to be really hot. He was heavy set, very strong looking, the sort of body type you would expect on someone who worked out but also had a bit of insulation over the muscle. He was pretty darn hot in my opinion. We had never hooked up or met before, he was a complete stranger. We met on Grindr, and I had wanted to hook up with a guy for a long time, but never had the courage. This guy was hot and pretty open so I finally said what the heck.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began on Grindr and we were both rather shy about it but obviously needed the sex. We chatted, exchanged pics. and told each other what we were comfortable with, what we expected. I believe I instigated it because of the face/body/dick pics he sent. He was pretty glorious, and his cock was the perfect type: well-shaped head, very thick at the base, which sloped up to his 7 inches. I was a bit scared but I had been practicing with a dildo of the same size… and let’s be honest I couldn’t resist the thought of having that dick inside me. So I told him I wanted him to fuck me ASAP and gave him my address.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? It was my first ever hook up, and my first ever experience with a guy, so I was pretty darn nervous. It was a quiet night, so when I heard a car drive up to my building, I knew it was him. He knocked and I opened the door, and then showed him into my bedroom. I honestly don’t remember if there was much small talk. I think he went to the bathroom and came back in, but I don’t really remember cause I was so nervous (not like nervous in a ‘I want this to stop way’ just nervous because I mean, who wouldn’t be). We kind of stood there awkwardly for a moment, and then he just reached out and started massaging my crotch. I was surprised (I didn’t know how all this worked) but I was moaning before too long. I didn’t want this to be about me though; I wanted to experiment with him and do what he wanted. So I reached out to return the favor, putting both hands on his crotch and started to feel for him, stroking when I found him through his jeans. I didn’t have very good leverage through jeans though, so we quickly moved to the bed. He was on his back taking off his pants and underwear (can’t remember if he took off his socks) but as soon as he was free from his underwear, I got above him and started stroking. I couldn’t believe my luck: his body was just as thick and strong as they looked in the pics, and his cock was just as glorious. The thought of having someone taller than me, stronger than me, with a bigger cock than me, got me all sorts of flustered. I kept stroking him, switching hands as I was on all fours above him on the bed. At some point I took all my clothes off, I don’t remember when, but once I was naked, I knew I wanted to do more. We had discussed protection, so I took a condom from him and put it on, and began blowing him. I know oral with a condom isn’t as good, so as soon as I thought I was able I started to deep throat him. At this point he got pretty verbal, started cursing, and put his hands on my head. He didn’t really need to do anything, as I was already fucking my own face into his crotch, but he still kept both hands on my head. I had ‘practice’ but wasn’t a pro, so I gagged a little when my lips went to his base, and things got a little messy as I continued to deep throat him. As my throat started to get sore, I got up on my knees above him and grabbed some lube from the nightstand. I lubed up his cock with my hand and then guided him into me, at first we were both frantically fucking each other, but after a while he slowed down and just kinda rolled his hips while I did most of the work. At this point he started playing with my cock, which was bouncing on his belly. It was kinda hard, but not really, so he stroked me until I got hard, and after I was hard, he just kind of held his hand there and made me hump his hand and belly. I didn’t really realize it at first, but I was fucking myself on his cock and also humping his hand/belly in the same motion. It made me feel really submissive and a bit humiliated, and I got really into it, frantically fucking myself on his cock and hand. I was moaning and cursing a ton, and I leaned back to put one hand on his leg to give me better leverage, I really fucked myself on him then, and I came all over his hand and belly. It felt so good and it made me feel really truly submissive.

I asked him if I could take a break as I was pretty spent, and he said yeah of course (he hadn’t cum yet). After about 15 minutes (I think I just quietly dozed a bit while he spooned me) he started to finger fuck me, gently, trying to get me back in the mood. I knew I had gotten off and he didn’t so I owed him (you never owe anyone sex, but the idea turned me on at the time). I started to moan and push my butt back onto his hand, signaling I was ready. I told him I wanted to be fucked doggy style, he said okay and flipped me onto my stomach, a bit impatient I guess. He took a spare pillow and put it under my waist, and pushed me down so everything but my waist and hips were in contact with the mattress. He pulled up my waist a little bit and reached around to pull my semi hard cock down and back, so it was resting behind the pillow where he could see it. He lubed his fingers and finger fucked me for a bit, then he put lube on his cock before putting a new condom on, and lubed his cock and pushed inside me. I was still obviously very willing, and he wanted to get his rocks off pretty bad, so he began to fuck me furiously. Sometimes he would lay on top of me and fuck me into the bed, other times he would kneel behind me and pull my hips up to meet his thrusts. He fucked me for a really long time, he always thrust down to his base, and always seemed to hit my prostate/g-spot. It felt so good, different than cumming from my cock. I didn’t actually cum from my ass but I felt a very intense pressure deep inside me when he was fucking me. I hadn’t been fucked like that before so I was moaning and raising my hips to meet him towards the end. After a while of this fucking, he started to get erratic, shorter deeper thrusts, and he told me he was going to cum. I just pressed my hips into him and felt his body jerk, he was grunting and cursing in my ear as he came. I was too far gone to actually feel his cock shoot his cum (if that’s a thing) but when he pulled out of my ass his condom had a good sized load in it. I was very proud of myself.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I don’t remember much about the rest of that night, but we exchanged numbers and fucked once more about a week later. The second time I wasn’t as vocal, and I think that was a deal breaker for him, as he didn’t respond next time I asked for a booty call. I would gladly let this guy fuck me again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To feel more confident, Submission / Relinquishing power, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My best friends, a bi guy and ace/demi girl. They were super psyched and excited for me to have my first experience with a guy. They also kinda liked the detailed version 🙂

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? My first experience with a guy, and the fact that I learned I really really liked being submissive in the bedroom.

What was the WORST thing about this hookup? It didn’t happen again 🙁

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Totally. I’m more positive about hook ups and casual sex, I don’t look down on or slut shame other people.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? Pretty awesome 🙂

You have a hookup story to share? Submit it here!